Highly Efficient and Practical N-Heterocyclic Carbene Organocatalyzed Chemoselective N-1/C-3-Functionalization of Isatins with Green Chemistry Principles
DC Field | Value | Language |
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dc.contributor.author | Mudithanapelli, Chandrashekar | - |
dc.contributor.author | Vasam, Chandra Sekhar | - |
dc.contributor.author | Vadde, Ravinder | - |
dc.contributor.author | Kim, Mi-hyun | - |
dc.date.available | 2020-02-27T08:41:33Z | - |
dc.date.created | 2020-02-06 | - |
dc.date.issued | 2018-12 | - |
dc.identifier.issn | 2470-1343 | - |
dc.identifier.uri | https://scholarworks.bwise.kr/gachon/handle/2020.sw.gachon/3035 | - |
dc.description.abstract | Ecofriendly N-heterocyclic carbene (NHC) organocatalysis can control the N-1-functionalization (aza-Michael addition) and C-3-functionalization (Morita-Baylis-Hillman reaction, MBH) of isatins in the absence of (1) a protecting group, (2) a stoichiometric reagent, and (3) heat energy. The challengeable N-1-functionalization of N-unsubstituted isatins into N-substituted (NS) isatins was realized through 10 mol % NHC and 10 mol % 1,8-diazabicyclo[5.4.0] undec-7-ene catalysts within 10 min with up to 98% isolation yield. The subsequent MBH adducts of as-synthesized NS-isatins (N-1/C-3-functionalization) was perfectly acquired in 10 mol % NHC and 10 mol % 1,4-diazabicyclo[2.2.2] octane catalysis within 30 min with superiority to C-3/N-1-functionalization (MBH/aza-Michael). For guiding the application to a versatile druggable isatin library, the NHC catalysis was compared with reported functionalization of isatins in view of green chemistry principles including solvent scoring of ACS GCI pharmaceutical roundtable, E-factor, atom economy, and so on. | - |
dc.language | 영어 | - |
dc.language.iso | en | - |
dc.publisher | AMER CHEMICAL SOC | - |
dc.relation.isPartOf | ACS OMEGA | - |
dc.subject | TO-TAIL DIMERIZATION | - |
dc.subject | MICHAEL ADDITION | - |
dc.subject | METAL-FREE | - |
dc.subject | DERIVATIVES | - |
dc.subject | ESTERS | - |
dc.subject | ENALS | - |
dc.subject | ACID | - |
dc.subject | NUCLEOPHILICITY | - |
dc.subject | OXINDOLES | - |
dc.subject | UMPOLUNG | - |
dc.title | Highly Efficient and Practical N-Heterocyclic Carbene Organocatalyzed Chemoselective N-1/C-3-Functionalization of Isatins with Green Chemistry Principles | - |
dc.type | Article | - |
dc.type.rims | ART | - |
dc.description.journalClass | 1 | - |
dc.identifier.wosid | 000454244600136 | - |
dc.identifier.doi | 10.1021/acsomega.8b02361 | - |
dc.identifier.bibliographicCitation | ACS OMEGA, v.3, no.12, pp.17646 - 17655 | - |
dc.identifier.scopusid | 2-s2.0-85058798655 | - |
dc.citation.endPage | 17655 | - |
dc.citation.startPage | 17646 | - |
dc.citation.title | ACS OMEGA | - |
dc.citation.volume | 3 | - |
dc.citation.number | 12 | - |
dc.contributor.affiliatedAuthor | Mudithanapelli, Chandrashekar | - |
dc.contributor.affiliatedAuthor | Kim, Mi-hyun | - |
dc.type.docType | Article | - |
dc.subject.keywordPlus | TO-TAIL DIMERIZATION | - |
dc.subject.keywordPlus | MICHAEL ADDITION | - |
dc.subject.keywordPlus | METAL-FREE | - |
dc.subject.keywordPlus | DERIVATIVES | - |
dc.subject.keywordPlus | ESTERS | - |
dc.subject.keywordPlus | ENALS | - |
dc.subject.keywordPlus | ACID | - |
dc.subject.keywordPlus | NUCLEOPHILICITY | - |
dc.subject.keywordPlus | OXINDOLES | - |
dc.subject.keywordPlus | UMPOLUNG | - |
dc.relation.journalResearchArea | Chemistry | - |
dc.relation.journalWebOfScienceCategory | Chemistry, Multidisciplinary | - |
dc.description.journalRegisteredClass | scie | - |
dc.description.journalRegisteredClass | scopus | - |
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